VP of Sales

Vice President of Sales

Location : Flexible / Remote Compensation : $150$185k base + competitive OTE, strong equity, and comprehensive benefits

About Overalls

Overalls is on a mission to transform how people experience benefits and support at work. We're building a category-defining company, and we're now ready to accelerate growth with the right sales leadership.

We're looking for a Vice President of Sales to help Overalls evolve from a founder-led sales motion to a predictable and repeatable revenue engine. This is a high-impact leadership role on our executive team, where you'll both sell directly and lay the foundation for a world-class sales organization that takes us to the next stage of growth.

What You'll Do

• Own the sales motion : Transition Overalls from founder-led selling to a scalable, repeatable sales process.
• Be hands-on early : Act as an individual contributor in the near-term, driving deals while building the playbook for scale.
• Design the sales framework : Introduce and instill best practices from proven models like MEDDIC, Challenger Sales, SPIN, or others you've mastered.
• Build the team : Recruit, mentor, and lead a sales team over timesetting structure, process, and culture.
• Drive predictable growth : Establish pipeline discipline, forecasting accuracy, and performance metrics that align with company goals.
• Be our sales SME : Serve as the company's subject matter expert on all things sales strategy, training, and enablement.
• Deeply understand the buyer : Lead sales into HR and benefits decision-makers, while expanding our footprint into insurance carriers, unions, and associations.

What We're Looking For

Why Join Us